Method for producing diphenylmethane derivative

A method for producing a compound of the following Formula 1b, the method comprising the steps of:

• (1) reacting a compound of the following Formula 2 with a compound of the following Formula 3 and subjecting the resultant to a cyclization reaction, to obtain a compound of the following Formula 4;
• (2) subjecting the compound of Formula 4 to aldehydation or amidation, followed by reacting the resultant with the compound of Formula 5 and performing reduction, to obtain a compound of the following Formula 6;
• (3) reacting the compound of Formula 6 with a compound of the following Formula 8 and then performing reduction, to obtain a compound of the following Formula 9;
• (4) forming a furanose ring of the compound of Formula 9 into a pyranose ring under an acidic condition and then introducing a protecting group thereinto, to obtain a compound of the following Formula 10;
• and
• (5) treating the compound of Formula 10 with thiourea, reacting the resultant with C1-7 alkyl halide, and then performing reduction,
• in the formulae,
• R is C1-7 alkylthio;
• n is 1 or 2;
• PG is a protecting group;
• X′ is halogen or C1-7 alkyl;
• X, Y, and Hal are each independently halogen;
• B is
• in which Ra, Rb, Rc, and Rd are each independently hydrogen, halogen, hydroxy, mercapto, cyano, nitro, amino, carboxy, oxo, C1-7 alkyl, C1-7 alkylthio, C2-7 alkenyl, C2-7 alkynyl, C1-7 alkoxy, C1-7 alkoxy-C1-7 alkyl, C2-7 alkenyl-C1-7 alkyloxy, C2-7 alkynyl-C1-7 alkyloxy, C3-10 cycloalkyl, C3-7 cycloalkylthio, C5-10 cycloalkenyl, C3-10 cycloalkyloxy, C3-10 cycloalkyloxy-C1-7 alkoxy, phenyl-C1-7 alkyl, C1-7 alkylthio-phenyl, phenyl-C1-7 alkoxy, mono- or di-C1-7 alkylamino, mono- or di-C1-7 alkylamino-C1-7 alkyl, C1-7alkanoyl, C1-7alkanoylamino, C1-7 alkylcarbonyl, C1-7 alkoxycarbonyl, carbarmoyl, mono- or di-C1-7 alkylcarbamoyl, C1-7 alkylsulfonylamino, phenylsulfonylamino, C1-7 alkylsulfinyl, C6-14 arylsulfonyl, C6-14 arylsulfonyl, C6-14 aryl, 5- to 13-membered heteroaryl, 5- to 10-membered heterocycloalkyl, 5- to 10-membered heterocycloalkyl-C1-7 alkyl, or 5- to 10-membered heterocycloalkyl-C1-7 alkoxy;
• a ring C is C3-10 cycloalkyl, C5-10 cycloalkenyl, C6-14 aryl, 5- to 13-membered heteroaryl, or 5- to 10-membered heterocycloalkyl;
• the alkyl, alkenyl, alkynyl, and alkoxy are each independently unsubstituted, or have one or more substituents selected from the group consisting of halogen, hydroxy, cyano, nitro, amino, mercapto, C1-7 alkyl, and C2-7 alkynyl;
• the cycloalkyl, cycloalkenyl, aryl, heteroaryl, and heterocycloalkyl are each independently unsubstituted, or have one or more substituents selected from the group consisting of halogen, hydroxy, cyano, nitro, amino, mercapto, C1-4 alkyl, and C1-4 alkoxy;
• and
• the heteroaryl and heterocycloalkyl each independently contain one or more heteroatoms selected from the group consisting of N, S, and O.